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Preparative asymmetric synthesis of canonical and non-canonical α-amino acids through formal enantioselective biocatalytic amination of carboxylic acids

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논문

Preparative asymmetric synthesis of canonical and non-canonical α-amino acids through formal enantioselective biocatalytic amination of carboxylic acids

학술지

Advanced synthesis & catalysis

저자명

Dennig, Alexander; Blaschke, Fabio; Gandomkar, Somayyeh; Tassano, Erika; Nidetzky, Bernd

초록

<P><B>Abstract</B></P><P>Chemical and biocatalytic synthesis of non&#8208;canonical &alpha;&#8208;amino acids (ncAAs) from renewable feedstocks and using mild reaction conditions has not efficiently been solved. Here, we show the development of a three&#8208;step, scalable and modular one&#8208;pot biocascade for linear conversion of renewable fatty acids (FAs) into enantiopure <SMALL>l</SMALL>&#8208;&alpha;&#8208;amino acids. In module 1, selective &alpha;&#8208;hydroxylation of FAs is catalyzed by the P450 peroxygenase P450<SUB>CLA</SUB>. By using an automated H<SUB>2</SUB>O<SUB>2</SUB> supplementation system, efficient conversion (46 to >99%; TTN>3300) of a broad range of FAs (C6:0 to C16:0) into valuable &alpha;&#8208;hydroxy acids (&alpha;&#8208;HAs; >90% &alpha;&#8208;selective) is shown on preparative scale (up to 2.3 g L<SUP>&minus;1</SUP> isolated product). In module 2, a redox&#8208;neutral hydrogen borrowing cascade (alcohol dehydrogenase/amino acid dehydrogenase) allowed further conversion of &alpha;&#8208;HAs into <SMALL>l</SMALL>&#8208;&alpha;&#8208;AAs (20 to 99%). Enantiopure <SMALL>l</SMALL>&#8208;&alpha;&#8208;AAs (e.e. >99%) including the pharma synthon <SMALL>l</SMALL>&#8208;homo&#8208;phenylalanine can be obtained at product titers of up to 2.5 g L<SUP>&minus;1</SUP>. Based on renewables and excellent atom economy, this biocascade is among the shortest and greenest synthetic routes to structurally diverse and industrially relevant ncAAs.</P>

발행연도

2019

ISSN

1615-4150

ISSN

1615-4169

361

6

페이지

pp.1348-1358

주제어

catalysis; fatty acid; amino acid; P450; biocascade

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1 2023-12-11

논문; 2019-12-31

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